CN1082968C - 基于含硫尿烷的树脂组合物,其树脂,光学元件以及包括该树脂的透镜 - Google Patents
基于含硫尿烷的树脂组合物,其树脂,光学元件以及包括该树脂的透镜 Download PDFInfo
- Publication number
- CN1082968C CN1082968C CN96110926A CN96110926A CN1082968C CN 1082968 C CN1082968 C CN 1082968C CN 96110926 A CN96110926 A CN 96110926A CN 96110926 A CN96110926 A CN 96110926A CN 1082968 C CN1082968 C CN 1082968C
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- Prior art keywords
- compound
- lens
- resin
- sulfydryl
- benzene
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- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Expired - Lifetime
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- 229910052717 sulfur Inorganic materials 0.000 title claims abstract description 35
- 239000011593 sulfur Substances 0.000 title claims abstract description 34
- JOYRKODLDBILNP-UHFFFAOYSA-N Ethyl urethane Chemical compound CCOC(N)=O JOYRKODLDBILNP-UHFFFAOYSA-N 0.000 title claims abstract description 32
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- 229920005989 resin Polymers 0.000 title claims description 57
- 230000003287 optical effect Effects 0.000 title claims description 44
- 239000011342 resin composition Substances 0.000 title abstract 3
- -1 (thio) cyanate compound Chemical class 0.000 claims abstract description 238
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- 238000006116 polymerization reaction Methods 0.000 claims description 26
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 25
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- 125000000524 functional group Chemical group 0.000 claims description 5
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- 125000004185 ester group Chemical group 0.000 description 11
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- 239000005864 Sulphur Substances 0.000 description 10
- XXROGKLTLUQVRX-UHFFFAOYSA-N allyl alcohol Chemical compound OCC=C XXROGKLTLUQVRX-UHFFFAOYSA-N 0.000 description 10
- UENWRTRMUIOCKN-UHFFFAOYSA-N benzyl thiol Chemical compound SCC1=CC=CC=C1 UENWRTRMUIOCKN-UHFFFAOYSA-N 0.000 description 10
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- 125000001931 aliphatic group Chemical group 0.000 description 9
- 230000000052 comparative effect Effects 0.000 description 9
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- NSBVMRLTDBAOBT-UHFFFAOYSA-N disulfanylmethylbenzene Chemical compound SSCC1=CC=CC=C1 NSBVMRLTDBAOBT-UHFFFAOYSA-N 0.000 description 9
- 150000002513 isocyanates Chemical class 0.000 description 9
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- FERIUCNNQQJTOY-UHFFFAOYSA-N Butyric acid Chemical compound CCCC(O)=O FERIUCNNQQJTOY-UHFFFAOYSA-N 0.000 description 8
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical class OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 8
- DHKHKXVYLBGOIT-UHFFFAOYSA-N acetaldehyde Diethyl Acetal Natural products CCOC(C)OCC DHKHKXVYLBGOIT-UHFFFAOYSA-N 0.000 description 8
- 238000012986 modification Methods 0.000 description 8
- OFBQJSOFQDEBGM-UHFFFAOYSA-N n-pentane Natural products CCCCC OFBQJSOFQDEBGM-UHFFFAOYSA-N 0.000 description 8
- 229910052757 nitrogen Inorganic materials 0.000 description 8
- 229910000073 phosphorus hydride Inorganic materials 0.000 description 8
- 229920003023 plastic Polymers 0.000 description 8
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- 125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 description 7
- UPMLOUAZCHDJJD-UHFFFAOYSA-N 4,4'-Diphenylmethane Diisocyanate Chemical compound C1=CC(N=C=O)=CC=C1CC1=CC=C(N=C=O)C=C1 UPMLOUAZCHDJJD-UHFFFAOYSA-N 0.000 description 7
- XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 description 7
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- 125000002228 disulfide group Chemical group 0.000 description 7
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- 239000000243 solution Substances 0.000 description 7
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- JKJWYKGYGWOAHT-UHFFFAOYSA-N bis(prop-2-enyl) carbonate Chemical compound C=CCOC(=O)OCC=C JKJWYKGYGWOAHT-UHFFFAOYSA-N 0.000 description 1
- 230000031709 bromination Effects 0.000 description 1
- 238000005893 bromination reaction Methods 0.000 description 1
- 125000001246 bromo group Chemical group Br* 0.000 description 1
- MGZLGROFYWKSCQ-UHFFFAOYSA-N butane-1,2,3-trithiol Chemical compound CC(S)C(S)CS MGZLGROFYWKSCQ-UHFFFAOYSA-N 0.000 description 1
- 235000019437 butane-1,3-diol Nutrition 0.000 description 1
- IAQRGUVFOMOMEM-UHFFFAOYSA-N butene Natural products CC=CC IAQRGUVFOMOMEM-UHFFFAOYSA-N 0.000 description 1
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- YYRMJZQKEFZXMX-UHFFFAOYSA-N calcium;phosphoric acid Chemical compound [Ca+2].OP(O)(O)=O.OP(O)(O)=O YYRMJZQKEFZXMX-UHFFFAOYSA-N 0.000 description 1
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 description 1
- 150000001244 carboxylic acid anhydrides Chemical class 0.000 description 1
- 125000001309 chloro group Chemical group Cl* 0.000 description 1
- 125000004218 chloromethyl group Chemical group [H]C([H])(Cl)* 0.000 description 1
- 239000011248 coating agent Substances 0.000 description 1
- 238000000576 coating method Methods 0.000 description 1
- 238000000748 compression moulding Methods 0.000 description 1
- 238000009833 condensation Methods 0.000 description 1
- 230000005494 condensation Effects 0.000 description 1
- 230000001143 conditioned effect Effects 0.000 description 1
- 239000004643 cyanate ester Substances 0.000 description 1
- 125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 description 1
- 125000004851 cyclopentylmethyl group Chemical group C1(CCCC1)C* 0.000 description 1
- NNBZCPXTIHJBJL-UHFFFAOYSA-N decalin Chemical compound C1CCCC2CCCCC21 NNBZCPXTIHJBJL-UHFFFAOYSA-N 0.000 description 1
- 238000007033 dehydrochlorination reaction Methods 0.000 description 1
- TXCDCPKCNAJMEE-UHFFFAOYSA-N dibenzofuran Chemical compound C1=CC=C2C3=CC=CC=C3OC2=C1 TXCDCPKCNAJMEE-UHFFFAOYSA-N 0.000 description 1
- GYZLOYUZLJXAJU-UHFFFAOYSA-N diglycidyl ether Chemical compound C1OC1COCC1CO1 GYZLOYUZLJXAJU-UHFFFAOYSA-N 0.000 description 1
- 239000000539 dimer Substances 0.000 description 1
- HTDKEJXHILZNPP-UHFFFAOYSA-N dioctyl hydrogen phosphate Chemical compound CCCCCCCCOP(O)(=O)OCCCCCCCC HTDKEJXHILZNPP-UHFFFAOYSA-N 0.000 description 1
- 150000002009 diols Chemical class 0.000 description 1
- 150000004862 dioxolanes Chemical class 0.000 description 1
- LTYMSROWYAPPGB-UHFFFAOYSA-N diphenyl sulfide Chemical compound C=1C=CC=CC=1SC1=CC=CC=C1 LTYMSROWYAPPGB-UHFFFAOYSA-N 0.000 description 1
- KZTYYGOKRVBIMI-UHFFFAOYSA-N diphenyl sulfone Chemical compound C=1C=CC=CC=1S(=O)(=O)C1=CC=CC=C1 KZTYYGOKRVBIMI-UHFFFAOYSA-N 0.000 description 1
- CZZYITDELCSZES-UHFFFAOYSA-N diphenylmethane Chemical compound C=1C=CC=CC=1CC1=CC=CC=C1 CZZYITDELCSZES-UHFFFAOYSA-N 0.000 description 1
- YENZEWKLSIXGBO-UHFFFAOYSA-N disulfanylethane Chemical compound CCSS YENZEWKLSIXGBO-UHFFFAOYSA-N 0.000 description 1
- 150000002019 disulfides Chemical class 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 238000005516 engineering process Methods 0.000 description 1
- 238000005886 esterification reaction Methods 0.000 description 1
- LDLDYFCCDKENPD-UHFFFAOYSA-N ethenylcyclohexane Chemical compound C=CC1CCCCC1 LDLDYFCCDKENPD-UHFFFAOYSA-N 0.000 description 1
- 125000001301 ethoxy group Chemical group [H]C([H])([H])C([H])([H])O* 0.000 description 1
- MKVYSRNJLWTVIK-UHFFFAOYSA-N ethyl carbamate;2-methylprop-2-enoic acid Chemical compound CCOC(N)=O.CC(=C)C(O)=O.CC(=C)C(O)=O MKVYSRNJLWTVIK-UHFFFAOYSA-N 0.000 description 1
- WUDNUHPRLBTKOJ-UHFFFAOYSA-N ethyl isocyanate Chemical compound CCN=C=O WUDNUHPRLBTKOJ-UHFFFAOYSA-N 0.000 description 1
- FKRCODPIKNYEAC-UHFFFAOYSA-N ethyl propionate Chemical compound CCOC(=O)CC FKRCODPIKNYEAC-UHFFFAOYSA-N 0.000 description 1
- 210000003746 feather Anatomy 0.000 description 1
- 239000000945 filler Substances 0.000 description 1
- 244000144992 flock Species 0.000 description 1
- 238000013467 fragmentation Methods 0.000 description 1
- 238000006062 fragmentation reaction Methods 0.000 description 1
- 150000002240 furans Chemical class 0.000 description 1
- XXMIOPMDWAUFGU-UHFFFAOYSA-N hexane-1,6-diol Chemical compound OCCCCCCO XXMIOPMDWAUFGU-UHFFFAOYSA-N 0.000 description 1
- 229940051250 hexylene glycol Drugs 0.000 description 1
- 238000002347 injection Methods 0.000 description 1
- 239000007924 injection Substances 0.000 description 1
- 125000000654 isopropylidene group Chemical group C(C)(C)=* 0.000 description 1
- 150000002540 isothiocyanates Chemical group 0.000 description 1
- 150000002576 ketones Chemical class 0.000 description 1
- 125000005647 linker group Chemical group 0.000 description 1
- FPYJFEHAWHCUMM-UHFFFAOYSA-N maleic anhydride Chemical compound O=C1OC(=O)C=C1 FPYJFEHAWHCUMM-UHFFFAOYSA-N 0.000 description 1
- JDSHMPZPIAZGSV-UHFFFAOYSA-N melamine Chemical compound NC1=NC(N)=NC(N)=N1 JDSHMPZPIAZGSV-UHFFFAOYSA-N 0.000 description 1
- 239000003595 mist Substances 0.000 description 1
- 238000002156 mixing Methods 0.000 description 1
- 238000000465 moulding Methods 0.000 description 1
- XAUGWFWQVYXATQ-UHFFFAOYSA-N n-phenylbenzenesulfonamide Chemical compound C=1C=CC=CC=1S(=O)(=O)NC1=CC=CC=C1 XAUGWFWQVYXATQ-UHFFFAOYSA-N 0.000 description 1
- 150000002847 norbornane derivatives Chemical class 0.000 description 1
- JRZJOMJEPLMPRA-UHFFFAOYSA-N olefin Natural products CCCCCCCC=C JRZJOMJEPLMPRA-UHFFFAOYSA-N 0.000 description 1
- RFPMGSKVEAUNMZ-UHFFFAOYSA-N pentylidene Chemical group [CH2+]CCC[CH-] RFPMGSKVEAUNMZ-UHFFFAOYSA-N 0.000 description 1
- 150000002989 phenols Chemical class 0.000 description 1
- LYXOWKPVTCPORE-UHFFFAOYSA-N phenyl-(4-phenylphenyl)methanone Chemical compound C=1C=C(C=2C=CC=CC=2)C=CC=1C(=O)C1=CC=CC=C1 LYXOWKPVTCPORE-UHFFFAOYSA-N 0.000 description 1
- 125000000843 phenylene group Chemical group C1(=C(C=CC=C1)*)* 0.000 description 1
- 208000026435 phlegm Diseases 0.000 description 1
- 239000003504 photosensitizing agent Substances 0.000 description 1
- 230000000704 physical effect Effects 0.000 description 1
- 229920003229 poly(methyl methacrylate) Polymers 0.000 description 1
- 229920001281 polyalkylene Polymers 0.000 description 1
- 229920000573 polyethylene Polymers 0.000 description 1
- 239000005056 polyisocyanate Substances 0.000 description 1
- 229920001228 polyisocyanate Polymers 0.000 description 1
- 230000000379 polymerizing effect Effects 0.000 description 1
- 229920000098 polyolefin Polymers 0.000 description 1
- 229920000915 polyvinyl chloride Polymers 0.000 description 1
- KHESWBSVXIUTTH-UHFFFAOYSA-N prop-2-enoic acid;4,5,6-trihydroxy-2-methylhex-1-en-3-one Chemical compound OC(=O)C=C.CC(=C)C(=O)C(O)C(O)CO KHESWBSVXIUTTH-UHFFFAOYSA-N 0.000 description 1
- FAIDIRVMPHBRLT-UHFFFAOYSA-N propane-1,2,3-triol;prop-2-enoic acid Chemical compound OC(=O)C=C.OC(=O)C=C.OCC(O)CO FAIDIRVMPHBRLT-UHFFFAOYSA-N 0.000 description 1
- 235000019260 propionic acid Nutrition 0.000 description 1
- IUVKMZGDUIUOCP-BTNSXGMBSA-N quinbolone Chemical compound O([C@H]1CC[C@H]2[C@H]3[C@@H]([C@]4(C=CC(=O)C=C4CC3)C)CC[C@@]21C)C1=CCCC1 IUVKMZGDUIUOCP-BTNSXGMBSA-N 0.000 description 1
- 230000005855 radiation Effects 0.000 description 1
- 239000007870 radical polymerization initiator Substances 0.000 description 1
- 150000003254 radicals Chemical class 0.000 description 1
- 230000036632 reaction speed Effects 0.000 description 1
- YGSDEFSMJLZEOE-UHFFFAOYSA-M salicylate Chemical compound OC1=CC=CC=C1C([O-])=O YGSDEFSMJLZEOE-UHFFFAOYSA-M 0.000 description 1
- 229960001860 salicylate Drugs 0.000 description 1
- 125000005504 styryl group Chemical group 0.000 description 1
- RINCXYDBBGOEEQ-UHFFFAOYSA-N succinic anhydride Chemical compound O=C1CCC(=O)O1 RINCXYDBBGOEEQ-UHFFFAOYSA-N 0.000 description 1
- WTSBJMAOQNCZBF-UHFFFAOYSA-N sulfanylmethylsulfanylmethanethiol Chemical compound SCSCS WTSBJMAOQNCZBF-UHFFFAOYSA-N 0.000 description 1
- 125000000475 sulfinyl group Chemical group [*:2]S([*:1])=O 0.000 description 1
- 150000003457 sulfones Chemical class 0.000 description 1
- 150000003459 sulfonic acid esters Chemical class 0.000 description 1
- 125000004434 sulfur atom Chemical group 0.000 description 1
- 238000005987 sulfurization reaction Methods 0.000 description 1
- 239000002426 superphosphate Substances 0.000 description 1
- ISXSCDLOGDJUNJ-UHFFFAOYSA-N tert-butyl prop-2-enoate Chemical compound CC(C)(C)OC(=O)C=C ISXSCDLOGDJUNJ-UHFFFAOYSA-N 0.000 description 1
- RAOIDOHSFRTOEL-UHFFFAOYSA-N tetrahydrothiophene Chemical compound C1CCSC1 RAOIDOHSFRTOEL-UHFFFAOYSA-N 0.000 description 1
- 229920002803 thermoplastic polyurethane Polymers 0.000 description 1
- UVZICZIVKIMRNE-UHFFFAOYSA-N thiodiacetic acid Chemical compound OC(=O)CSCC(O)=O UVZICZIVKIMRNE-UHFFFAOYSA-N 0.000 description 1
- WFKWXMTUELFFGS-UHFFFAOYSA-N tungsten Chemical compound [W] WFKWXMTUELFFGS-UHFFFAOYSA-N 0.000 description 1
- 229910052721 tungsten Inorganic materials 0.000 description 1
- 239000010937 tungsten Substances 0.000 description 1
- AVWRKZWQTYIKIY-UHFFFAOYSA-N ureidocarboxylic acid Natural products NC(=O)NC(O)=O AVWRKZWQTYIKIY-UHFFFAOYSA-N 0.000 description 1
- 150000003673 urethanes Chemical class 0.000 description 1
- KAKZBPTYRLMSJV-UHFFFAOYSA-N vinyl-ethylene Natural products C=CC=C KAKZBPTYRLMSJV-UHFFFAOYSA-N 0.000 description 1
- 238000005303 weighing Methods 0.000 description 1
- 229910052724 xenon Inorganic materials 0.000 description 1
- FHNFHKCVQCLJFQ-UHFFFAOYSA-N xenon atom Chemical compound [Xe] FHNFHKCVQCLJFQ-UHFFFAOYSA-N 0.000 description 1
- 239000008096 xylene Substances 0.000 description 1
- 238000004383 yellowing Methods 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G18/00—Polymeric products of isocyanates or isothiocyanates
- C08G18/06—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen
- C08G18/28—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen characterised by the compounds used containing active hydrogen
- C08G18/30—Low-molecular-weight compounds
- C08G18/38—Low-molecular-weight compounds having heteroatoms other than oxygen
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G18/00—Polymeric products of isocyanates or isothiocyanates
- C08G18/06—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen
- C08G18/28—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen characterised by the compounds used containing active hydrogen
- C08G18/67—Unsaturated compounds having active hydrogen
- C08G18/675—Low-molecular-weight compounds
- C08G18/677—Low-molecular-weight compounds containing heteroatoms other than oxygen and the nitrogen of primary or secondary amino groups
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G18/00—Polymeric products of isocyanates or isothiocyanates
- C08G18/06—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen
- C08G18/28—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen characterised by the compounds used containing active hydrogen
- C08G18/30—Low-molecular-weight compounds
- C08G18/38—Low-molecular-weight compounds having heteroatoms other than oxygen
- C08G18/3855—Low-molecular-weight compounds having heteroatoms other than oxygen having sulfur
- C08G18/3876—Low-molecular-weight compounds having heteroatoms other than oxygen having sulfur containing mercapto groups
-
- G—PHYSICS
- G02—OPTICS
- G02B—OPTICAL ELEMENTS, SYSTEMS OR APPARATUS
- G02B1/00—Optical elements characterised by the material of which they are made; Optical coatings for optical elements
- G02B1/04—Optical elements characterised by the material of which they are made; Optical coatings for optical elements made of organic materials, e.g. plastics
- G02B1/041—Lenses
Landscapes
- Chemical & Material Sciences (AREA)
- Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Organic Chemistry (AREA)
- Physics & Mathematics (AREA)
- General Physics & Mathematics (AREA)
- Optics & Photonics (AREA)
- Polyurethanes Or Polyureas (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP165284/95 | 1995-06-30 | ||
| JP16528495 | 1995-06-30 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| CN1148055A CN1148055A (zh) | 1997-04-23 |
| CN1082968C true CN1082968C (zh) | 2002-04-17 |
Family
ID=15809413
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CN96110926A Expired - Lifetime CN1082968C (zh) | 1995-06-30 | 1996-06-29 | 基于含硫尿烷的树脂组合物,其树脂,光学元件以及包括该树脂的透镜 |
Country Status (6)
| Country | Link |
|---|---|
| US (1) | US5736609A (enrdf_load_stackoverflow) |
| EP (1) | EP0751161B1 (enrdf_load_stackoverflow) |
| KR (1) | KR100222194B1 (enrdf_load_stackoverflow) |
| CN (1) | CN1082968C (enrdf_load_stackoverflow) |
| AU (1) | AU691416B2 (enrdf_load_stackoverflow) |
| DE (1) | DE69625550T2 (enrdf_load_stackoverflow) |
Families Citing this family (27)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US6008296A (en) | 1995-04-19 | 1999-12-28 | Optima, Inc. | Optical terpolymer of polyisocyanate, polythiol and polyene monomers |
| US5955206A (en) * | 1995-05-12 | 1999-09-21 | Mitsui Chemicals, Inc. | Polysulfide-based resin composition, polysulfide-based resin, and optical material comprising the resin |
| JP3974668B2 (ja) * | 1995-10-24 | 2007-09-12 | 株式会社アサヒオプティカル | 高屈折率眼鏡用プラスチックレンズ |
| US5908876A (en) * | 1996-04-19 | 1999-06-01 | Mitsui Chemicals, Inc. | Optical resin composition comprising a thiourethane prepolymer and use thereof |
| JP3300610B2 (ja) * | 1996-08-14 | 2002-07-08 | 旭光学工業株式会社 | 紫外線硬化性組成物 |
| DE69836523T2 (de) * | 1997-02-21 | 2007-10-04 | Mitsui Chemicals, Inc. | Verfahren zur herstellung eines selenisierten transparenten optischen materials |
| FR2773162B1 (fr) * | 1997-12-29 | 2000-02-11 | Essilor Int | Composition photopolymerisable a base de monomeres polyiso (thio)cyanates et de monomeres a proton labile, comprenant un agent photoamorceur et un agent d'activation de la photopolymerisation et artciles d'optique obtenus |
| US7258437B2 (en) | 2005-09-07 | 2007-08-21 | Transitions Optical, Inc. | Photochromic multifocal optical article |
| US8017193B1 (en) * | 2008-08-06 | 2011-09-13 | Hrl Laboratories, Llc | Monomeric formulation for making polymer waveguides |
| KR101074450B1 (ko) * | 2008-12-29 | 2011-10-17 | 주식회사 케이오씨솔루션 | 신규 티올 화합물을 이용한 광학렌즈용 경량성 고굴절 수지조성물 및 이를 이용한 광학렌즈 |
| IT1397438B1 (it) | 2009-12-30 | 2013-01-10 | Comau Spa | Installazione per l'assemblaggio di parti meccaniche su scocche di autoveicoli |
| BR112013016183B1 (pt) * | 2010-12-27 | 2020-03-24 | Mitsubishi Gas Chemical Company, Inc. | Composição para material óptico e material óptico |
| KR101289908B1 (ko) * | 2011-04-22 | 2013-07-26 | 주식회사 우노켐 | 비닐 모노머와 황화합물의 부가 반응을 이용한 수지 조성물 및 이를 이용한 광학 모노머 제조 |
| WO2012176439A1 (ja) * | 2011-06-23 | 2012-12-27 | 三井化学株式会社 | 重合性組成物 |
| EP2850114B1 (en) * | 2012-05-18 | 2017-03-15 | Ricoh Company, Ltd. | Photopolymerizable composition, photopolymerizable inkjet ink, and ink cartridge |
| JP5373226B1 (ja) * | 2012-08-14 | 2013-12-18 | 三井化学株式会社 | ポリチオール組成物、光学材料用重合性組成物およびその用途 |
| JP6228599B2 (ja) * | 2013-05-24 | 2017-11-08 | 株式会社ブリヂストン | 接着剤、接着シート及び積層体 |
| KR20160143671A (ko) | 2014-04-11 | 2016-12-14 | 코베스트로 도이칠란트 아게 | 투명한 폴리티오우레탄 물품을 제조하기 위한 방향족 니트릴을 함유하는 조성물 |
| TWI615415B (zh) * | 2016-09-13 | 2018-02-21 | 奇美實業股份有限公司 | 光學材料用樹脂組成物、光學材料用樹脂及其所形成的光學透鏡 |
| KR102029256B1 (ko) * | 2017-09-28 | 2019-11-29 | 에스케이씨 주식회사 | 플라스틱 렌즈용 중합성 조성물 |
| JPWO2020004531A1 (ja) * | 2018-06-29 | 2021-07-08 | ホヤ レンズ タイランド リミテッドＨＯＹＡ Ｌｅｎｓ Ｔｈａｉｌａｎｄ Ｌｔｄ | 光学部材用重合性組成物、光学部材および光学部材の製造方法 |
| JPWO2020004534A1 (ja) * | 2018-06-29 | 2021-06-24 | ホヤ レンズ タイランド リミテッドＨＯＹＡ Ｌｅｎｓ Ｔｈａｉｌａｎｄ Ｌｔｄ | 光学部材用硬化物および光学部材 |
| JP7296754B2 (ja) * | 2019-03-28 | 2023-06-23 | ホヤ レンズ タイランド リミテッド | 光学部材用重合性組成物、光学部材、及び眼鏡レンズ |
| JP2021167399A (ja) * | 2020-04-13 | 2021-10-21 | ホヤ レンズ タイランド リミテッドHOYA Lens Thailand Ltd | 光学材料用重合性組成物の製造方法、透明樹脂の製造方法、およびレンズ基材の製造方法 |
| KR102391162B1 (ko) | 2020-10-05 | 2022-04-26 | 에스케이씨 주식회사 | 접합용 필름 및 이를 포함하는 광투과 적층체 |
| KR102252498B1 (ko) | 2020-10-05 | 2021-05-13 | 에스케이씨 주식회사 | 티오우레탄층을 포함하는 필름, 티오우레탄층 제조용 조성물 및 이들의 제조방법 |
| CN114379178B (zh) | 2020-10-05 | 2023-05-12 | Skc株式会社 | 玻璃接合用薄膜、薄膜的制备方法以及透光层叠体 |
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|---|---|---|---|---|
| JPS525240A (en) * | 1975-07-02 | 1977-01-14 | Toshiba Corp | Signal compensator of high frequency amplifier |
| US4668713A (en) * | 1984-12-21 | 1987-05-26 | Loctite (Ireland) Limited | Conformal coating systems |
| EP0490778A1 (fr) * | 1990-12-14 | 1992-06-17 | Rhone-Poulenc Chimie | Composés soufrés et polymères obtenus à partir de ces composés soufrés |
| EP0659790A1 (en) * | 1993-12-20 | 1995-06-28 | MITSUI TOATSU CHEMICALS, Inc. | High-speed polymerizable resin composition and lenses obtained therefrom |
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| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPH0525240A (ja) * | 1991-07-19 | 1993-02-02 | Mitsubishi Rayon Co Ltd | プラスチツクレンズ用組成物 |
| JP3279848B2 (ja) * | 1993-12-20 | 2002-04-30 | 三井化学株式会社 | 高速重合性樹脂組成物およびレンズ |
-
1996
- 1996-06-14 US US08/663,734 patent/US5736609A/en not_active Expired - Lifetime
- 1996-06-18 AU AU56015/96A patent/AU691416B2/en not_active Expired
- 1996-06-19 DE DE69625550T patent/DE69625550T2/de not_active Expired - Lifetime
- 1996-06-19 EP EP96304557A patent/EP0751161B1/en not_active Expired - Lifetime
- 1996-06-29 KR KR1019960025704A patent/KR100222194B1/ko not_active Expired - Lifetime
- 1996-06-29 CN CN96110926A patent/CN1082968C/zh not_active Expired - Lifetime
Patent Citations (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS525240A (en) * | 1975-07-02 | 1977-01-14 | Toshiba Corp | Signal compensator of high frequency amplifier |
| US4668713A (en) * | 1984-12-21 | 1987-05-26 | Loctite (Ireland) Limited | Conformal coating systems |
| EP0490778A1 (fr) * | 1990-12-14 | 1992-06-17 | Rhone-Poulenc Chimie | Composés soufrés et polymères obtenus à partir de ces composés soufrés |
| EP0659790A1 (en) * | 1993-12-20 | 1995-06-28 | MITSUI TOATSU CHEMICALS, Inc. | High-speed polymerizable resin composition and lenses obtained therefrom |
Also Published As
| Publication number | Publication date |
|---|---|
| EP0751161A2 (en) | 1997-01-02 |
| AU5601596A (en) | 1997-01-16 |
| DE69625550D1 (de) | 2003-02-06 |
| KR970001460A (ko) | 1997-01-24 |
| AU691416B2 (en) | 1998-05-14 |
| US5736609A (en) | 1998-04-07 |
| CN1148055A (zh) | 1997-04-23 |
| EP0751161A3 (enrdf_load_stackoverflow) | 1997-02-05 |
| EP0751161B1 (en) | 2003-01-02 |
| DE69625550T2 (de) | 2003-11-13 |
| KR100222194B1 (ko) | 1999-10-01 |
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